4,7-bis{4-[5-hexyl-2-(triisopropylsilylethynyl)-3-thienyl]phenyl}-2-methylbenzo[b]thiophene

Base Information

• Chemical Name: 4,7-bis{4-[5-hexyl-2-(triisopropylsilylethynyl)-3-thienyl]phenyl}-2-methylbenzo[b]thiophene
• CAS No.: 1391908-43-2
• Molecular Formula: C₆₃H₈₄S₃Si₂
• Molecular Weight: 993.729
• Mol file: 1391908-43-2.mol

Synonyms:4,7-bis{4-[5-hexyl-2-(triisopropylsilylethynyl)-3-thienyl]phenyl}-2-methylbenzo[b]thiophene

Chemical Property of 4,7-bis{4-[5-hexyl-2-(triisopropylsilylethynyl)-3-thienyl]phenyl}-2-methylbenzo[b]thiophene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,7-bis{4-[5-hexyl-2-(triisopropylsilylethynyl)-3-thienyl]phenyl}-2-methylbenzo[b]thiophene

There total 16 articles about 4,7-bis{4-[5-hexyl-2-(triisopropylsilylethynyl)-3-thienyl]phenyl}-2-methylbenzo[b]thiophene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 58.0%

2-(4-{5-hexyl-2-[2-(triisopropylsilyl)ethynyl]-3-thienyl}phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1333949-72-6) + 4,7-dibromo-2-methylbenzo[b]thiophene (1391908-24-9) → 4,7-bis{4-[5-hexyl-2-(triisopropylsilylethynyl)-3-thienyl]phenyl}-2-methylbenzo[b]thiophene (1391908-43-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,4-dioxane; water; at 90 ℃; for 13h; Inert atmosphere;

DOI:10.1246/bcsj.20100345

Reference yield: 17.0%

2-(4-{5-hexyl-2-[2-(triisopropylsilyl)ethynyl]-3-thienyl}phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1333949-72-6) + 4,7-dibromo-2-methylbenzo[b]thiophene (1391908-24-9) → 4-bromo-7-{4-[5-hexyl-2-(triisopropylsilylethynyl)-3-thienyl]phenyl}-2-methylbenzo[b]thiophene (1391908-33-0) + C36H45BrS2Si (1391908-32-9) + 4,7-bis{4-[5-hexyl-2-(triisopropylsilylethynyl)-3-thienyl]phenyl}-2-methylbenzo[b]thiophene (1391908-43-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,4-dioxane; water; at 90 ℃; for 13h; Inert atmosphere;

DOI:10.1246/bcsj.20100345

Reference yield:

3,6-dibromo-2-fluorobenzaldehyde (870703-68-7) → 4,7-bis{4-[5-hexyl-2-(triisopropylsilylethynyl)-3-thienyl]phenyl}-2-methylbenzo[b]thiophene (1391908-43-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

1.2: 7 h / -30 °C / Inert atmosphere

2.1: potassium carbonate / methanol / 2 h / 0 - 20 °C / Inert atmosphere

3.1: gold(I) chloride / 1,4-dioxane; water / 0.17 h / 20 °C / Inert atmosphere

4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere

4.2: 15 h / -78 - 20 °C / Inert atmosphere

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 13 h / 90 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; potassium carbonate; gold(I) chloride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.20100345

upstream raw materials:

3,6-dibromo-2-fluorobenzaldehyde

2-(4-{5-hexyl-2-[2-(triisopropylsilyl)ethynyl]-3-thienyl}phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4,7-dibromo-2-methylbenzo[b]thiophene

3,6-dibromo-2-(t-butylsulfanyl)(ethynyl)benzene